Hydroquinone → 4-(6'-Methyloctyloxy)phenol

HRID 986098Notes

Reaction equation

HRID 986098 reaction equation
[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2].Br[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH:15]([CH3:18])[CH2:16][CH3:17].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:18][CH:15]([CH2:16][CH3:17])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][O:2][C:1]1[CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 785HydroquinoneHCID 11430Potassium CarbonateHCID 135481051-Bromo-6-methyloctane

Product 1

HCID 230392144-(6'-Methyloctyloxy)phenol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 25 ml-flask was charged with 0.637 g of hydroquinone, 1 g of optically active 1-bromo-6-methyloctane, 0.667 g of anhydrous potassium carbonate and 4 ml of N,N-dimethylformamide, and reaction was carried out at 90° C. for 9.5 hours. After the reaction, insoluble substances were recovered by filtration and extracted with ether. The ether layer was washed with water and a saturated aqueous solution of sodium chloride and dried, and ether was removed by distillation under reduced pressure. The obtained crude product was purified by silica gel chromatography to obtain 0.32 g of optically active 4-(6'-methyloctyloxy)phenol.

Workup

  1. customAfter the reaction, insoluble substances
  2. filtrationwere recovered by filtration
  3. extractionextracted with ether
  4. washThe ether layer was washed with water
  5. dry with materiala saturated aqueous solution of sodium chloride and dried
  6. customether was removed by distillation under reduced pressure
  7. customThe obtained crude product
  8. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-c9ba37f1d3f84863bd1d24e907df54ec
Source dataset
uspto-grants-1987_12
Patent number
US04710585

Reaction notes

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